


Milo’s Princess Pounding

by SexTheHex



Category: Super Mario & Related Fandoms
Genre: Demons, F/M, Futa on Male, Futanari, Multi
Language: English
Status: Completed
Published: 2019-04-15
Updated: 2019-04-15
Packaged: 2020-01-13 13:11:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,061
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18469642
Author URL: https://archiveofourown.org/users/SexTheHex/pseuds/SexTheHex
Summary: Milo’s last mission was a little below his normal quota. He needs to take in a bit more spunk for his next encounter! Can Milo and his big new bouncy breasts drain three hung princesses totally dry?





	Milo’s Princess Pounding

**Author's Note:**

> This fic stars Takumi.exe's incubus femboy Milo! This a sequel to the older piece I uploaded with him here. You can check him and his creator out here: https://twitter.com/takumi_exe/status/1109132954268241922

“Ms. Rojo, I’m sorry!” Milo pleaded.

“I get the budget to let you fuck all these people from far away worlds and you STILL can’t gather up enough spunk!?” Milo’s boss yelled.

Poor Milo somehow hadn’t collected enough jizz in his previous encounter with two hung futa ladies. Three quarts was the minimum collection amount for a job well done. Oh, but Milo seemed to have spent just a bit too long on the ground letting cum ooze out his gaping asshole last mission. When his final semen consumption was tallied up, Milo totalled to… 2.9971 quarts downed! Unacceptable!

Rojo slammed her fist on her desk. “Failure is a very serious issue when it comes to the many machinations of Pantheon. Deploying to a location and failing to collect enough semen deserves reprimanding; no ifs, ands, or butts!”

Milo clasped his hands together and begged. “Please! Have mercy! Can I just-”

Discipline came swiftly once it’d been concluded Milo had fallen short. Failure to collect enough semen with his current body meant modifications to get him to that point. Before Milo could ask his boss to round up just this once, he could feel his body changing. Something like a chest cramp suddenly sat in, as if something was wrong with that toned slim chest of his. Oh, but momentary chest pain was the worst of Milo’s worries once he saw what that tingle truly was; he had the wrath of future back pain to worry about Now he could see it, now he could look down and stare at his own flesh surge and blossom into something undeniably feminine. Tits! Milo had grown tits! Oh, what sort of Incubus had tits!? This was humiliating!

“This should arouse your partners more next time you extract from them. Don’t fail me again or they may just be a permanent staple of your anatomy.” Rojo barked.

“I don’t need this!” Milo defiantly announced, hands sizing up and already playing with his big boisterous knockers. “It was a freak accident, I’ll never collect that little again!”

“For your sake I hope you’re right!” Rojo thundered. “Further such incompetence will not be tolerated! Now, get back to work!”

Milo continued to protest profusely at his boss, tits jiggling away, as Rojo extended a hand towards him. Mid-bitching, a flaming pentagram etched its signet into the floor below before glowing black with some evil energy. It all came bursting forth in one mighty geyser, completely consuming Milo! And, just like that, it he was gone. Milo had teleported away to his next assignment worlds and worlds away.

 

* * *

 

 

“You’ve got to show up to tea more often, Daisy!” Peach celebrated. “I have to say, your… your “cream” adds such a distinct flavor to the tea~”

Rosalina extended her teacup forward, letting the mixture of herbal team and the trio’s steaming hot spunk pour into her cup. “And so much too! I never thought anyone would be able to compete with Peach’s fire hose, but you’re almost there with a couple inches extra!”

Daisy looked as please as could be at her friend’s compliments. “All you had to do was tell me you guys had these weekly jerk off sessions! I would have been happy to spend the afternoon fapping and fucking with you two!

Nothing quite beat an hour of furiously masturbating and frotting together with friends than hydrating with quality tea in their proper clothes. Yes, Peach always seemed to bring the finest tea bags from exotic kingdoms to these little get togethers… most claiming to be an efficient way to refill their tea bags with their potent aphrodisiac properties. All it really needed was a bit of a salty twang to it to dress up the taste. Homegrown Sarasaland spunk straight from the source seemed to be the perfect additive to make their little relaxation sessions something special. Already the trio could feel their enormous, throbbing royal septurs getting primed for action all over again!

As the first half of their tea downed the princess trio’s throats, a pillar of black light thundered out of the floor in the room. The three watched in startled amazement as some unknown hellish magic unfolded right before their eyes!

Milo stood in the center of that light pillar as it all finally faded out. He started up, still continuing the conversation with his boss. “I’ve got an ass this big and you think I need boobs too!? You’re a total…”

Milo wasn’t facing his boss anymore. No, he was facing a wall. A look behind him and his newest three targets came into view, each one staring with hanging mouths at his plump femboy incubus bottom. Tiny thumps could be heard as Peach and Rosalina’s erections violently sprung to full mast against the table. A blunt, heavier one came right after as Daisy’s monstercock joined the others.

“Oh… oh my!” Peach gasped. “I think we might have summoned a succubus by accident, dears!”

“Oh dear. Was our masturbating together so sinful we summoned a demon? My, they’ll be half a dozen here by the end of the night then…” Rosalina mulled over.

“Ladies, I think she sort of just… showed up? I don’t think we did anything wrong.” Daisy started. “And… wow! Wait, it’s a guy, look at the face! Look between his legs! He’s an incubus with tits!”

The trio laughed, leaving Milo to smolder. Urgh, people first guessing he was a succubus always sucked! Why did they always assume he was a girl? ...Not that his fat ass helped much. Oh, and especially with his new tits it got a bit weird, but he still had a right to get angry!

“HEY!” Milo’s shrill voice cried out. “I’m a demon! A mighty incubus who’s come to purge your bodies of your succulent life force for the wrath of Hell’s evil! You should fear me you skanks! Prepare to-”

Milo’s lame attempt at a speech to make cum slurping sound imposing was interrupted by the shuffle of chairs and giddy chatter as the princesses stood up. At first, their words were merely drowning the boy’s declaration out. Once Milo saw their unmistakable erect cock bulges though, he fell silent. Oh… oh my god, were they that big? How the hell was he going to take anything like that inside him!?

The princesses chatter was hard to make out as Milo’s mind fixated on the swaying girl rods draped just beneath their dresses. He heard bits and parts of it. Stuff like “dresses” and “pretty” and “make up” and “proper”... It was all a bit hard to take in with his mind fantasizing about dicks, and quashing said fantasy trying to reaffirm that he totally wasn’t going to be a willing cum dump for people this rude.

Peach, Daisy, and Rosalina all seemed intent on teaching him how exactly all that cockmeat was going to fit in him. The trio moved in. Milo expected their assault to be underwhelming; that these dainty feminine princess were as weak as their fancy dresses implied. That absolutely wasn’t the case. As the trio gripped onto his body with iron strength, Milo felt like a total puppet in their clutches! These ladies were strong as could be from marathon smashing outside their queenly duties. Milo couldn’t do anything but let the trio move him as they pleased!

“Hey! Get your hands off me you skanks!” Milo shouted. “A demon won’t be overpowered this easily! Step back or I’ll-”

“Or what? You’ll suck our dicks? Yeah we know, sweetie. Succubi don’t have much of a line of defense besides that.” Daisy taunted.

Peach began rattling off at that remark. “Oh, and you haven’t sucked a cock proper until you’ve been under my wing! I’ve been in every position you can think of! Sucking dicks that stretch your jaw, taking other ladies down to my nuts, autofillation… You’ll be a cocksucking princess in no time with a bit of help from yours truly!”

With Daisy at Milo’s bottom, Rosalina holding on to his midsection, and Peach holding his head, there was little opportunity for Milo to make any counter action. Before he knew it, he was on his back and on the ground, pinned beneath the weight of the tall and heavy rosalina sitting on his stomach. Peach got straight to work following through on her claims of experience.

Dresses ruffled and waistbands snapped aside. In one swift motion, Peach’s pussy pounder was unleashed and ready for action! Her throbbing length looked enormous, well bigger than Milo’s own and on par with the largest lengths he’d ever have stuffed in his body! How was this all on a pretty princess like her? AAH! And it was already getting closer!

Forward Peach’s rod thrusted until her warm cockhead was pressed against Milo’s pouting lips. He absolutely wasn’t going to make it easy to fit that in there! A tight shut mouth, clenched teeth… these were all the defenses Milo planned on sporting in the face of this well hung lady’s monster cock. Yet, instead, his mouth went limp and his jaw opened wide to allow this woman’s titanic length to ravage his throat. Soon her whole length was sliding into his maw, her taunt, virile sperm banks coming closer to masking his face. Why wasn’t his body responding in defiance to these rude women!? He needed to find some inner strength to resist them before he had to take an intoxicating snort of Peach’s nuts just for air and… oh. Damn. He needed air now. Might as well take a deep breath pinned against the woman’s massive balls.

All the while, pent up Rosalina stood atop the incubus bottom’s body, primed to play with those freshly grown boy breasts. Her hands sunk into that succulent flesh, groping his new womanhood with total focus and adoration. It took little time for a third protrusion of hers to want to join her two hands in on the fun. Before long, her stirring cock bulge was begging to come out and make a woman out of Milo’s chest.

“Of course, when a princess has big slutty udders like yours on her chest…” Rosalina started, taking her own massive erect phallus out of her panties. “It’s her duty to share her wealth with the people! You’re devoting your life to your kingdom, devoting your body too is a natural step forward!”

Rosalina’s hands pressed Milo’s big bimbo breasts together to form a firm enough pussy for her to properly pound it. Titfucking had a certain knack to it that was hard to master; though Rosalina’s planet-sized tits usually did the job well! As soon as the pressure was just right, Rosey got to pumping Milo’s chest, sliding her even larger length into Milo’s makeshift orifice.Before long, Rosalina’s bright red cock head was coming out the other side of Milo’s breasts, just centimeters away from tapping his chin with a bead of her pre cum. Perhaps he’d have noticed; if Peach wasn’t violently fucking his face to the point of drawing most all his attention. All Milo could really feel of Rosey’s action was something hot, sweaty, and affectionate pressing in between his huge breasts.Oh, but he was quick to learn. His hands moved up and pressed his breasts together so Rosalina could pull all her effort in plowing his tit pussy instead.

Pleasing cocks with his face and using his chest for others’ pleasure… Milo was learning how to be a proper princess in so little time! That resistance towards these women as being nasty was fading away the more familiar he became with their expansive, throbbing kingdoms. With the work of this princess trio, he’s surely be a proper lady in no time. There was just one bit to this training left. One proper last action to turn Milo from a princess in training in the midst of a gang bang to a proper anal queen.

Daisy moved in closer. She pried Milo’s legs apart and pulled down his underwear to expose his naked rump. Oh, what an ass! Daisy had hardly seen a fat butt this fit for fucking on porn stars, let alone a guy! The princess simply couldn’t help but smack and squeeze that bubbly bottom like the proper plaything it was. Just about every inch of it begged to be bred and properly fucked.

Daisy hiked up her dress and let her absolute anaconda of a cock come up for air. As thick as a soda can and as long as her damn forearm, there was no denying Daisy was the finest cock in any of these Princesses’ kingdoms. Few clients Milo had ever dealt with had the sheer might Daisy was packing between her thighs. Even the hellish dicks back home seemed a little modest compared to the ass-stretching, butt-breaking, anal bitch-making mass of all natural girl cock Daisy was wielding. It was time to teach Milo what exactly queen sized meant.

Even with Peach pumping his throat, Milo could absolutely feel Daisy’s anal assault begin. What felt like a cool hand dabbled in lube pressed against his pucker… then what felt like someone’s knuckles. It took a while to actually realize the lubricant-doused protrusion on Milo’s asshole wasn’t a hand, but a full goddamn cock! The shock was enough to send him gasping… which ultimately just resulted in Peach’s precum backwashing out the corners of his mouth.

“And most important of all, the royal hierarchy depends on which lady has the biggest, thickest dick!” Daisy announced. “And if you’re not sporting the largest rod of all your peers, remember you’re a total bottom bitch who should always be primed for a royal ass fucking! I’m going to teach you some manners, boy! I’m going to stretch your ass until you’ve got anal etiquette down pat!

More and more of Daisy’s fat shaft steadily worked its way in, giving Milo a crash course on what exactly a proper dick was. Inch by inch it steadily worked its way in, claiming Milo’s makeshift pussy in the name of fat throbbing princess cocks. Milo continued to writh and twitch from the slowly sliding insertion, gurgling on Peach’s cock instead of yelping and moaning at being used like an onahole. It was quite the snug fit, so large and imposing in fact it felt like it simply wasn’t going to fit at all. Oh, but Daisy made it fit. Just the right amount of pressure and force and her cock slid deeper into the incubus bottom, deeper than he ever imagined that sort of thing could go!

She made it. Daisy shoved it in all the way. Her titanic ballsack was pressed against Milo’s bubbly cheeks, her full cock length was totally submerged in his tight warm insides! Milo couldn’t see it with Peach’s balls draped over his face and Rosalina on his chest, but it felt as if it was in his damn abdomen it was so deep. Indeed, from Daisy’s perspective, she could see Milo’s stomach bulge just a bit from her cock sinking so far inside him.

Now, it was time to paint his walls white.

Daisy adjusted her stance, wrapping Milo’s legs around her back and putting her weight in her hands. All that careful and meticulous insertion that Daisy had with her first thrust in left. Milo had been broken in, now Daisy could have some fun! Her monstrous pretty princess dick slid almost entirely out in one long thrust, pulling out until just the tip of her cockhead was submerged in Milo’s asshole. And then… SLAM! Down to the hilt! All in one authoritative, prostate pounding, butt-breaking thrust! And that was hardly the end of it. Out right back after, In right after that. Over and over and over again. Daisy was breeding that incubutt with all her strength!

Milo was absolutely drowning in hazey-minded cock drunkenness as the trio continued to fuck him stupid. All the most sensitive bits of his body were being totally assaulted by beautiful women with the most enormous cocks he’d ever stomached. Part of him wanted to still resist this trio for treating him like a joke. That part was rapidly fading away as the urge to go limp and let this trio do as they wish with him set in instead. Milo’s resolve finally caved as he felt the warmth of Daisy’s virile nuts press against his bottom. They could do whatever they wanted to him, so long as it meant more of this.

“A real lady has a total oral fixation!” Peach instructed. “We’ll make you a total cocksucking queen!”

“A real lady lets anyone and everyone grope her breasts!” Rosalina added. “We’re going to make your chest look so pretty in a nice dress!

“A real lady is a total spunk-loving anal whore!” Daisy exclaimed. “I’m gonna… Gonna… urgh-”

Milo’s tight asshole was too much for Daisy to bear. The girl switched into overdrive, treating Milo as nothing but a hole to be plowed! Climax was close. She wanted nothing more than to use Milo’s insides like the cum dumpster he was! She pumped hard. Fast. Ruthlessly! The other two joined pace and tried to reach that same peak with their darling mega-cocked alpha princess. They were going to drench this succu-boy slut!

“I’m g-gonna… gonna… Ur-UURRRRGH~!” Daisy groaned! This was it! Climax!

A huge glob of fresh girl jizz came spurting out of Daisy’s titanic girl cock right into the depths of Milo’s insides! Not one bit of the opening to his boypussy was spared; every square inch was positively painted in hot, potent princess putty! Poor Milo was bloated full in little time at all, excess cum seeping out of his asshole onto the carpet below. His insides were totally doused in the stuff, completely claimed in the name of Daisy’s royal scepter!

Rosalina and Peach scarcely had the resolve to stop themselves from cumming once their friend started writing in pleasure. It was time for them to bust their load over their busty demon slut as well. Rosalina tugged her meat out from between Milo’s cleavage to give her cock a few final wacks before she blew. Just like that, she was there! Her load went spraying everywhere, dousing Milo’s titties in a sticky film of girl jizz. Peach followed right after, sinking her length as deep as it could into Milo’s sluttly lips. Right down his esophagus the royal pink princess erupted, only withdrawing once she felt there was simply no space left. She withdrew her length and finished the job coating Milo’s mug in the last spurt of her enormous princess load.

“Oooh… Oh… Oh man.” Daisy sighed. “God, he’s totally built for this!”

“I’ll say!” Peach agreed. I didn’t know boys could even keep up with the wrath of one princess, let alone three!”

Rosalina loomed over the cumdumpster demon, smiling just like her princess sisterhood. “I think he’s passed our standards easily. We ought to make him a bit of an honorary princess. What do you say?”

 

* * *

 

 

Back in the depths of Pantheon, black light erupted out of the ground in front of Rojo’s desk. She put her pen down and awaited a status report from her incubus on how his last encounter had gone.

When the dust settled, Milo stood waiting and ready. Instead of his normal easy-going easy-access clothes, the boy was dolled up head to toe. A sparkling golden crown with sapphires and jades adorned his hair, down scrunched into a ponytail that trailed down past his neck. His eyes were dolled up with entirely too much mascara, with lips painted purple by some shining slick lipstick. An extravagant grey gown fit the boy, though with a few modification left for ideal play with princesses like the ones he’d just encountered. The cleavage of the outfit had a wide ovular boob window, perfect for groping Milo’s new pair of breasts at a moment’s notice. His hemline was far from a typical ballroom gowns to boot, stopping just a bit before his knees to allow upskirts and ass gropings as anyone pleased. Silky dark violet gloves and Sparkling grape heels rounded out the look, adding the perfect bit of contrast for the eyes as Milo bowed...

“Good morning Mistress Rojo!” Milo introduced himself, bowing polite as could be.

Rojo wasn’t sure what those clients did to Milo, but she could still see semen seeping down his thighs from his gaping asshole. As long as that trio were pumping him with enough spunk to cause that, Milo being a princess seemed fine enough...

 

* * *

 

 

“Really? Do you need it that bad~?” Peach asked.

“M-mhm!” Milo whimpered, hiking up his grey gown to expose his bottom.

“My my, Princess Milo! A princess is suppose to have more tact to their actions! Are you really so shameless to debase yourself in front of your peers?” Rosalina lectured.

Milo pulled the waistband to his panties down. “Yes ma’am…”

Daisy moved in, finally giving Milo the first taste of the attention he craved. Her hands slapped and spanked the boy’s plump princess bottom, cooing and giggling at delight at the sight of jiggling boy butt before her.

“So you want to be an anal queen again tonight right?” Daisy teased.

“Mhm…” Milo answered.

“You want to take all three of us again? Your poor little princess pucker so worn out you need the three of us spreading you open~?” Daisy persisted.

“P-please fuck me.” Milo panted.

“You greedy girl! You horny little pervert princess! Beg for it bitch!” Daisy yelled, slapping her prize.

“Fuck me!” Milo yelped.

“Louder!” Daisy demanded

“Fuck me!” Milo added.

“Own it bitch! Let us all know! Show us the real you!” Daisy laughed.

“Fuck me! FUCK ME! Shove all your fat dicks in me at once and pump my princess-hole until I’m cumming handsfree!” Milo screamed with all his heart!

The trio laughed. The trio huddled closer. Three firm rods of flesh slapped against the incubus boy’s fat bottom, slowly dragging their way towards the hungry gaping hole the three of them had ruined over months of ruthless assfucking. Nothing quite beat a night with their little demon anal princess. It was time to give him that triple dicked princess pounding he adored so much…

Visits to the Mushroom Kingdom tearoom proved to be a regular affair after Milo’s first encounter with the trio of princess ladies. They seemed to be a seemingly never ending source of spunk for Pantheon’s operations, and never seemed to tire of Milo’s visits at a moment’s notice. The trio even figured out the arcane magic associated with summoning a demon to ensure they always had someone ready for fun. Every other night it seemed they were ripping the demon out of hell to pleasure themselves with the feats of anal acrobatics only Milo seemed capable of.

And now came their favorite feat of the night. The trio kissing and groping one another, taking turns shoving their cocks in Milo’s gluttonous asshole and pumping him stupid. Nothing seemed to beat sinking into each others lips among a chorus of girly femboy moans and enthusiastic ass fucking, whatever cocks were idle feeling the heavenly stroke of her fellow princess’s soft hands. It was the perfect way to round things out after an evening totally filled with ruthless futanari sex. One final climax to rub in their royal dominance...

“I can’t believe it all fits in there!” Rosalina reacted. “Ooh, and it still feels so tight!”

“What a proper proud anal queen!” Peach celebrated. “Ooooh~! I’m almost there! Ready to cum ladies?”

“Sure am! Fuck, how does this greedy demon bitch even FIT three cocks this huge in his ass?” Daisy smirked. “Ahhh…. OOoooohh… Oh fuck, OH FUCK! I’m gonna blow girls! Let’s do it together!”

Milo’s eyes went wide and his voice turned to whimpers as the combined heft of three thick girlcocks over a full foot in length sunk near their entirety into his asshole. All three of them blew their loads in unison, pumping Milo’s gut with an unearthly amount of spunk to form what almost looked like a baby bump. God, it’d been hours now of this. Hours of fucking and sucking these ladies, trying to drain them dry of whatever they could offer.

Milo couldn’t wait to do it all again tomorrow.


End file.
